The Elder Scrollsfranchise is filled to the brim with interesting, and sometimes polarizing, characters with intriguing motivations. While there is a lot of buzz in the fandom about which character is the most hated or which character possesses brutality beyond others, and questions about power, method, and morality definitely come up often in the fandom, they do not often receive a consensus.
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Ruthlessness isa trait marked by the combination of all of these factorsand the characters within this list are defined as such in addition to the level of guilt they feel post the fact. In the interest of keeping this list fair, the Aedra and the Daedra will be disregarded due to their mythical status.
10Delphine - The Illusion Of Choice (The Elder Scrolls V: Skyrim)
Delphine is the leader of the Blades' faction in Skyrim. Once charged with guarding the rulers of Tamriel and beingknown as the Dragonguard, the Bladesin Skyrim hold not even a fraction of the power that they once did.
In a haste to return to this era of glory, Delphine, one of the two remaining Blades, sends the Dragonborn on a series of quests to get to the bottom of the Dragon attacks. By the end of the quest line, the player’s final quest is to kill the Dragon that has been helping them defeat Alduin, Paarthurnax.

9Astrid - Hail Sithis Till Convenient (The Elder Scrolls V: Skyrim)
Trained in the art of clandestine assassination, one will be hard-pressed to find anyone more ruthless thana member of the Dark Brotherhood.
Astrid, the leader of the Falkreath branch, refuses to defer to the authority of the Night Mother, plots behind the Dragonborn’s back to ultimately try and kill them off and does it for selfish reasons. The betrayal to the player comes at a great cost to the Dark Brotherhood itself as an unintended consequence of her actions. However, she admits guilt a few moments before her death.

8Mercer Frey - His Sleight of Hand (The Elder Scrolls V: Skyrim)
Mercer Frey is the leader ofthe Thieves Guild in Skyrim, and also serves as the main villain of the quest line. Unlike Astrid, the cutthroat seemingly has no amount of regret and proves this countless times.
Mercer’s ambitions were well-thought-out, and his cloak-and-dagger methods come as somewhat of a surprise at the quest line’s conflict. One can question if stealing from thieves is really all that immoral, but the leader had unmistakably crossed the code of the order and broke a lot of people’s trust with no regard.

7Maven Black-Briar - The Monopolist Matriarch (The Elder Scrolls V: Skyrim)
There are few characters who garner as much hate and antagonistic sentiment in the fan base as Maven Black-Briar herself, and this is for good reason too.
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She is incredibly self-serving, shrewd, cunning, and rude. What makes Maven ruthless is not her ability to kill competitors of her brewery business or anyone else in the Black-Briars' way, but that she seemingly has no qualms with committing such acts and has very little care for anyone who is not her family or herself.
6Lady Syl - The Mistress of Deception (The Elder Scrolls IV: Oblivion)
The Lady of Paranoia holds the court of Dementiain the Shivering Islesand is the more put-together of the two dukes. Lady Syl is explained to the player as a deeply overcautious person who thinks that everyone is trying to kill her.
However, if the player following that quest line denies helping her with weeding out the conspirators, she wastes no time in reminding them that she will stick them in her torture chamber. Like the ones preceding her on this list, treachery is another mark of the Duchess' ruthlessness as she gives herself over to Jyggalag and becomes a Priest of Order, betraying and spiting Lord Sheogorath.

5Matthieu Bellamont - Consumed By Madness and Grief (The Elder Scrolls IV: Oblivion)
InOblivion,the main antagonist of the Dark Brotherhood quest line is Matthieu Bellamont, a member of the Dark Brotherhood that has been serving the order since he was a young boy.
From allegedly killing his own father to gain the Night Mother’s attention, to systematically killing off members of the Dark Brotherhood, Bellamont had planned the downfall of the organization since his mother was murdered by a Dark Brotherhood assassin. This, though somewhat understandable and able to be rationalized, is a brutal act that characterizes a cold-blooded killer.

4Miraak - Betrayal for Ill-gotten Gains (The Elder Scrolls V: Skyrim)
Once a dragon priest, the “First Dragonborn"is an antagonist in the Dragonborn quest lineofSkyrim. He bound himself to Hermaeus Mora and his plane of Apocrypha gained all the knowledge and power that Hermaeus Mora offered, and then turned on his original masters, the Dragons.
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Despite all the power he had, he refused to end Alduin’s terror when asked by the Nords who pleaded with him to lend his expertise against the World Eater. The cherry on top is that when the player meets him after they have defeated Alduin, Miraak says that he could have done the deed on his own.
3Arch curate Vyrthur - Auri-El’s Unfavored (The Elder Scrolls V: Skyrim)
Arch curate Vyrthur isone of the last Snow Elvesin Skyrim. It is not a good sign that Gelebor, his brother, upon meeting the Dragonborn and Serana, requests that they kill Vyrthur due to the turpitude that the Falmer have brought on him.
Creating an entire prophecy, The Tyranny of The Sun, that would endanger the lives of countless people and throw Nirn into chaos, just to spite a Divine and derive some personal satisfaction for a wrong that perhaps was not even committed by said Divine is a product of his harmful vengeance.

2Mankar Camoran - The Instrument of Destruction (The Elder Scrolls IV: Oblivion)
Mankar Camoran is thecreator of the Mythic Dawn, a cult of Daedra worshipers in service to Mehrunes Dagon, the Lord of Destruction. Although his plane of Oblivion is called Mankar Camaron’s paradise, it is anything but.
Prisoners are getting harassed by Dremora, and the only way out of the plane is not even a true way out unless you have the Bands of the Chosen. It leads instead to a torture chamber. To add to his deeds of cruelty, he is the one who planned the assassination of the Emperor.

1Harkon - The Lord of The Volkihar Clan (The Elder Scrolls V: Skyrim)
In the Dawnguard quest line, the player meets the Volkihars,a court of powerful vampiresthat live far away from man and mer. Lord Harkon is the head of the Clan, and is by far the most ruthless character the Dragonborn meets in the game.
Not only does he betray the player and Serana, his daughter, but he also killed and sacrificed thousands of people as part of his worship to the Daedric Prince, Molag Bal. On top of that, Lord Harkon plots to follow the prophecy made by the Arch curate so that vampires can dominate Nirn and rule over it.


